Holiday rentals with a pool in Calvert County

Tranquility on Tilghman Island – Wide Water Views

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway. In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for

Spacious and private waterfront, sleeps 10

Are you looking for a family getaway or a peaceful location to telework? This property offers it all. Tastefully remodeled waterfront property with a large private salt water pool, dock for fishing, crabbing and kayaking. One-floor open plan with two large decks. Great for entertainment in privacy and is in proximity to restaurants, vineyards, beautiful beaches and parks of Chesapeake Bay and Patuxent River. Just 1 hour to the south of Washington DC and within minutes to NavAir base and Excelon

Luxury Farmette -Private & Secluded-1hr to DC

Plan your tranquil getaway to the countryside and escape to a luxury dream farmhouse. Located on 5 acres, the fully renovated home offers peace in a quiet, private location. Guests have access to a pool and outdoor shower, fire pit, a covered grilling area and a playground for children. The home is located approximately 1hr from Washington DC and is the perfect place for a retreat, family vacation and everything in between! Plenty of parking available for those traveling with boat/camper/RV.

Patuxent River View

Stay at this peaceful amenity rich guest house, perfectly located near North and Chesapeake Beaches and Herrington Harbor, with easy access to Washington, DC, Baltimore, & Annapolis. Enjoy a fully stocked kitchen, coffee and tea, fast WiFi, a seasonal pool, and a shaded gazebo—designed for comfort and convenience. Ideal for weddings, family visits, work trips, and quiet coastal retreats, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring.

Indoor pool/spa nestled in Southern Md. woods.

Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles).

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

Waterfront, pool, pickleball

Escape to this luxurious two-story waterfront home with two master suites, sleeping up to 12. Enjoy a gorgeous pool, large decks with scenic views, and a deep-water pier perfect for boating and fishing. Gather around the fire pit or stay active on the private pickleball and tennis court. Inside, spacious living areas offer comfort and style, ideal for families and groups. A serene retreat for relaxation and adventure alike. Book now for an unforgettable waterfront getaway!

Fire pit, pool, and chickens between D.C. and bay

Connect with family, friends and nature at this quiet one bedroom, one den apartment located in the DC metro area and minutes from Chesapeake Bay sports and fishing. Enjoy the outdoors in comfort! 🏊💦 In-ground Pool (1st Sat. May-1st Sat. Oct) 🔥🏕️ Fire pit 🔥🍔 Charcoal grill and picnic table poolside 🎥🍿 Disney Plus 🚙🚗 Free parking for up to two cars 🧑‍🧑‍🧒‍🧒🧑‍🧑‍🧒‍🧒 Private space for up to eight guests, including kids. 🐓🐥 Free Ranging Chicken Sightings

Private Country Escape • Spa • Fire Pit

Welcome to your private country escape—a spacious, inviting home designed for gathering, relaxing, and creating memories. Nestled in a quiet and very private neighborhood, this 5-bedroom, 3.5-bathroom retreat offers over 4,500 square feet of comfortable living space for up to 10 guests. Whether you’re reconnecting with family, spending quality time with friends, or working remotely in peaceful surroundings, this home offers everything you need for a memorable stay.

Tudor House Oasis

Welcome to your secluded retreat—this elegant 4‑bedroom, 3.5‑bath estate offers approximately 4,700 sq ft of upscale living space set on nearly 3 acres. Features include a 40 x 20 saltwater pool(June-September), hot tub, home theater, gourmet kitchen, and refined designer finishes throughout. 🏖 Beach Access: Chesapeake Beach, MD – ~10 miles North Beach, MD – ~11 miles 🛥 Solomons Island & Other Attractions Annapolis – ~30 miles Washington, D.C. – ~39 miles

Stunning North Beach Getaway w/ Inground Pool

Indulge in this beautifully appointed 4-bedroom, 2-bathroom house 6 blocks from the Chesapeake Bay boardwalk! Revel in a chef's kitchen, open living area, screened porch, with separate workspace. Relax by the heated saltwater pool BBQ on the deck or gather around the cozy firepit. Walk to restaurants and enjoy live music experiences, the local wine bar or beer, conveniently close to local wedding venues. This North Beach gem guarantees an unforgettable stay!

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).